Single-run capillary electrochromatographic analysis of hop acids and prenylated hop flavonoids

Vanhoenacker, Gerd; Dermaux, Anna; Keukeleire, Denis De; Sandra, Patrick

doi:10.1002/1615-9314(20010101)24:1<55::aid-jssc55>3.0.co;2-m

Cited by 20 publications

(7 citation statements)

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“…The prenylated flavanone 8-prenylnaringenin (8-PN) was recently isolated from the wood of the tropical tree Anaxagorea luzonensis (3) and also identified as the estrogenic component in hops (Humulus lupulus) and beer (4,5). As 8-PN was identified as the most potent phytoestrogen, it has become the subject of various research activities in chemistry (6), receptor binding and transactivation (7), plant biochemistry (8,9), in vitro pharmacology (3,(10)(11)(12)(13), and analytical methods (14)(15)(16)(17).…”

Section: Introductionmentioning

confidence: 99%

Development of a Radioimmunoassay for the Quantitative Determination of 8-Prenylnaringenin in Biological Matrices

Schaefer¹,

Bohlmann²,

Schleuning³

et al. 2005

J. Agric. Food Chem.

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Seven carboxylic acid haptens of 8-prenylnaringenin (8-PN) were synthesized, coupled to cationized bovine serum albumin, and employed to raise specific antisera in rabbits. Two linkers of different lengths (C3H6COOH and C6H12COOH) were coupled to the C7-OH group and separated into their respective enantiomers yielding the first four haptens. Racemic derivatives with C4'-OH coupled linkers C5H10COOH and C9H18COOH were synthesized carrying a methylated C7-OH. Another racemic C4'-OH hapten (CH2COOH) was prepared starting from naringenin. The haptens elicited variable antibody titers dependent on linker lengths, with short linkers giving the best results. Three antisera were characterized in detail: anti-C7-carboxy-propyloxy-2S-(-)-8-PN (anti-H-11), anti-C7-carboxy-propyloxy-2R-(+)-8-PN (anti-H-10), and anti-C4'-carboxy-methoxy-rac-8-PN (anti-H-25). anti-H-10 and anti-H-11 showed about 9% enantiomeric cross-reactivity, and anti-H-11 did not discriminate between isoxanthohumol (IX) and 8-PN (84% cross-reactivity). For anti-H-10, cross-reactivities in the range of 2-5% were found for xanthohumol, IX, and 6-prenylnaringenin. Respective numbers for anti-H-25 were 0.02, 0.1, and 0.2%. Tritiated 8-PN was synthesized yielding a 3H-tracer of high specific radioactivity (2.22 GBq/mg). A radioimmunoassay using anti-H-25 and 3H-8-PN was established and used for the quantitative determination of 8-PN in various beer brands and in the urine of six men after the consumption of three different brands of beer. Furthermore, the dose-dependent excretion of 8-PN was tested after the consumption of a higher volume of a single beer brand with and without spiking with 8-PN and a small oral dose of authentic 8-PN, respectively. Conflicting results led to a pilot test on the in vivo conversion (demethylation) of IX into 8-PN in two men. Conversion rates of 1.9 and 4.4% were estimated. Thus, the total 8-PN dose in beer brands spiced with natural hop or hop products seems to be the sum of the 8-PN amount in a consumed volume and the amount arising from the conversion of IX.

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Section: Introductionmentioning

confidence: 99%

Development of a Radioimmunoassay for the Quantitative Determination of 8-Prenylnaringenin in Biological Matrices

Schaefer¹,

Bohlmann²,

Schleuning³

et al. 2005

J. Agric. Food Chem.

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“…CEC including granular packed CEC 35, 43, 45, 72, 87, 96, monolithic CEC 42, 44, 97 and OT‐CEC 98, 99 analysis of flavanoids in different samples such as Humulus lupulus 72, Adinandra nitida 42, Citrus juices 43, Epimedium 35, corn 44, tea 45 and licorice 96 were developed (Table 1).…”

Section: Application Of Cec In Phytochemical Analysismentioning

confidence: 99%

CEC of phytochemical bioactive compounds

Yang

Zhao

2009

Electrophoresis

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Although there are many publications related to technological or methodological developments of CEC, few focus on the analysis of natural products, especially phytochemical bioactive compounds. This review summarized the application of CEC in the analysis of phytochemical bioactive components, including flavonoids, nucleosides, steroids, lignans, quinones and coumarins, as well as fingerprint analysis of herbs. The strategies for optimization of CEC conditions and detection were also discussed.

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“…A standard mixture containing the four major Rhubarb anthraquinones (aloe-emodin, emodin, chrysophanol, and physcion) was used for method optimization. Using a conventional C18 column, hop acids and prenylated flavonoids could be analyzed in a single run [73]. A simple sample pretreatment method was applied to avoid column contamination.…”

Section: 1 Polyphenolsmentioning

confidence: 99%

Recent applications of capillary electrochromatography

et al. 2001

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A review is presented of the most important recent applications of capillary electrochromatography (CEC) for the analysis of acidic, basic, and neutral compounds, of biomolecules, environmental substances, natural products, pharmaceuticals, and chiral compounds. Packed-column CEC (packed-CEC), open-tubular (OT-CEC), as well as pressure-assisted CEC (pseudo-CEC) are hereby considered. Papers published between July 1999 and April 2001 were taken into account. Applications before July 1999 have been reviewed in Electrophoresis 1999, 20, 3027-3065.

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Single-run capillary electrochromatographic analysis of hop acids and prenylated hop flavonoids

Cited by 20 publications

References 7 publications

Development of a Radioimmunoassay for the Quantitative Determination of 8-Prenylnaringenin in Biological Matrices

Development of a Radioimmunoassay for the Quantitative Determination of 8-Prenylnaringenin in Biological Matrices

CEC of phytochemical bioactive compounds

Recent applications of capillary electrochromatography

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